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Clarithromycin
drug data and news
Clarithromycin drug data, resources, and news articles (when available). Onconews.org provides news on cancer research. This section, which includes profiles on medicines that may or not be cancer-related is in beta form. If things run smoothly we will be releasing a new format late in the summer of 2006.
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| Generic name | Clarithromycin | ||
| Brand Names/Synonyms | Biaxin; Biaxin Xl; CAM; CLA; Clarithromycin; Clarithromycine; Clathromycin; Klacid; Klaricid; Macladin; Naxy; Prevpac; Veclam; Zeclar | ||
| Indication | For the treatment of Bacterial infection of (Pharyngitis/Tonsillitis, sinusitis, bronchitis, Pneumonia, Uncomplicated skin and skin structure infections ) caused by H.influenzae, M.catarrhalis, M.pneumoniae, S.pneumoniae, C.pneumoniae (TWAR), S.aureus, S | ||
| Sponsored links | Description | Not Available | |
| Pharmacology | Clarithromycin, a macrolide antibiotic similar to erythromycin and azithromycin, is effective against Mycobacterium avium complex (MAC) and is used for the treatment of Helicobacter pylori-associated peptic ulcer disease, community-acquired pneumonia, sinusitis, and chronic bronchitis. Clarithromycin is also used to treat respiratory tract, sexually transmitted, otitis media, and AIDS-related infections. | ||
| Mechanism Of Action | Clarithromycin is first metabolized to 14-OH clarithromycin. Like other macrolides, it then binds to the 50 S subunit of the 70 S ribosome of the bacteria, blocking RNA-mediated bacterial protein synthesis. Clarithromycin also inhibits the hepatic microsomal CYP3A4 isoenzyme and P-glycoprotein, an energy-dependent drug efflux pump. | ||
| Clarithromycin News (When available) |
CROI: Studies look at tipranavir/ritonavir's potency and ... Feb 28, 2006 ImQuest Gains Dual-Mechanism HIV Compounds From Samjin Feb 28, 2006 AIDS virus attacked inside & out Feb 7, 2006 CROI: etravirine (TMC125) and darunavir (TMC114) in treatment ... Feb 13, 2006 Tibotec pharmaceuticals ltd Feb 16, 2006 Positive Pre-Clinical Data on Two New Investigational HIV Fusion ... Feb 9, 2006 New Data on Tibotec HIV/AIDS Investigational Product Portfolio Feb 16, 2006 Positive Pre-Clinical Data on Two New Investigational HIV Fusion ... 09 Feb 2006 AIDS virus attacked inside & out Feb 7, 2006 COMUNICADO: Roche & Trimeris Select Two Next Generation HIV Fusion ... Jan 19, 2006 Roche and Trimeris Announce Selection of Two Next Generation HIV ... Jan 19, 2006 Roche and Trimeris Announce Selection of Two Next Generation HIV ... Jan 17, 2006 Tipranavir+Ritonavir Superior to Optimized Comparator Regimen in ... Dec 9, 2005 TNX-355 Poster Presentations at ICAAC Scheduled, Tanox to Host ... Dec 8, 2005 Boehringer Ingelheim Announces 48-Week Results from Aptivus(R) ... Nov 21, 2005 Boehringer Ingelheim Announces 48-Week Results from Aptivus(R) ... Nov 21, 2005 Tipranavir continues to show benefit in treatment-experienced ... Nov 30, 2005 New Study Shows Patients More Willing to Consider Self-Injectable ... Nov 18, 2005 FDA Issues Approvable Letter in Response to Application for Use of ... Nov 23, 2005 FDA Issues Approvable Letter in Response to Application for Use of ... Nov 24, 2005 Simplicity is the Key to Survival in the HIV Market where Older ... Nov 15, 2005 Follow-on Biological Products — Legal Issues Nov 15, 2005 Can latest advances in health psychology help improve HIV care? Nov 14, 2005 FDA Issues Approvable Letter in Response to Application for Use of ... Nov 23, 2005 International Approvals: Aptivus, Noxafil, Xolair 31 Oct 2005 Importance of the drug Fuzeon (enfuvirtide) in the management of ... Oct 20, 2005 New boosted PIs should be used with T-20 for maximum impact, say ... Oct 18, 2005 Tipranavir receives European marketing approval Oct 26, 2005 Tipranavir's EU Approval Provides a New Active Drug to be Combined ... Oct 26, 2005 HIV guidelines support use of drug Fuzeon Oct 17, 2005 Updated HIV/AIDS Treatment Guidelines Support Use of Fuzeon Plus ... Oct 13, 2005 Updated HIV/AIDS Treatment Guidelines Support Use of FUZEON Plus ... Oct 13, 2005 Influential HIV/AIDS Treatment Guidelines Support Use of FUZEON(R) ... Oct 14, 2005 New HIV guidelines support use of FUZEON® + active boosted PI for ... Oct 14, 2005 Influential HIV/AIDS Treatment Guidelines Support Use of FUZEON(R) ... Oct 14, 2005 Influential HIV/AIDS Treatment Guidelines Support Use of FUZEON(R) ... Oct 14, 2005 | ||
| Dosage Forms | suspension and tablets | ||
| Drug_Category | Anti-bacterial Agents; Other Macrolides; ATC:J01FA09 | ||
| Absorption | 50% | ||
| Interactions |
-->Interactions for Clarithromycin: Clarithromycin use in patients who are receiving theophylline may be associated with an increase of serum theophylline concentrations. Monitoring of serum theophylline concentrations should be considered for patients receiving high doses of theophylline or with baseline concentrations in the upper therapeutic range. In two studies in which theophylline was administered with clarithromycin (a theophylline sustained-release formulation was dosed at either 6.5 mg/kg or 12 mg/kg together with 250 or 500 mg q12h clarithromycin), the steady-state levels of Cmax, Cmin, and the area under the serum concentration time curve (AUC) of theophylline increased about 20%. Concomitant administration of single doses of clarithromycin and carbamazepine has been shown to result in increased plasma concentrations of carbamazepine. Blood level monitoring of carbamazepine may be considered. When clarithromycin and terfenadine were coadministered, plasma concentrations of the active acid metabolite of terfenadine were threefold higher, on average, than the values observed when terfenadine was administered alone. The pharmacokinetics of clarithromycin and the 14-hydroxy-clarithromycin were not significantly affected by coadministration of terfenadine once clarithromycin reached steady-state conditions. Concomitant administration of clarithromycin with terfenadine is contraindicated. Clarithromycin 500 mg every 8 hours was given in combination with omeprazole 40 mg daily to healthy adult subjects. The steady-state plasma concentrations of omeprazole were increased (Cmax, AUC0-24, and T½ increases of 30%, 89%, and 34%, respectively), by the concomitant administration of clarithromycin. The mean 24-hour gastric pH value was 5.2 when omeprazole was administered alone and 5.7 when co-administered with clarithromycin. Co-administration of clarithromycin with ranitidine bismuth citrate resulted in increased plasma ranitidine concentrations (57%), increased plasma bismuth trough concentrations (48%), and increased 14-hydroxy-clarithromycin plasma concentrations (31%). These effects are clinically insignificant. Simultaneous oral administration of clarithromycin and zidovudine to HIV-infected adult patients resulted in decreased steady-state zidovudine concentrations. When 500 mg of clarithromycin were administered twice daily, steady-state zidovudine AUC was reduced by a mean of 12% (n=4). Individual values ranged from a decrease of 34% to an increase of 14%. Based on limited data in 24 patients, when clarithromycin was administered two to four hours prior to oral zidovudine, the steady-state zidovudine Cmax was increased by approximately 2-fold, whereas the AUC was unaffected. Simultaneous administration of clarithromycin and didanosine to 12 HIV-infected adult patients resulted in no statistically significant change in didanosine pharmacokinetics. Concomitant administration of fluconazole 200 mg daily and clarithromycin 500 mg twice daily to 21 healthy volunteers led to increases in the mean steady-state clarithromycin Cmin and AUC of 33% and 18%, respectively. Steady-state concentrations of 14-OH clarithromycin were not significantly affected by concomitant administration of fluconazole. Concomitant administration of clarithromycin and ritonavir (n=22) resulted in a 77% increase in clarithromycin AUC and a 100% decrease in the AUC of 14-OH clarithromycin. Clarithromycin may be administered without dosage adjustment to patients with normal renal function taking ritonavir. However, for patients with renal impairment, the following dosage adjustments should be considered. For patients with CLCR 30 to 60 mg/min, the dose of clarithromycin should be reduced by 50%. For patients with CLCR < 30 ml/min, the dose of clarithromycin should be decreased by 75%. Spontaneous reports in the post-marketing period suggest that concomitant administration of clarithromycin and oral anticoagulants may potentiate the effects of the oral anticoagulants. Prothrombin times should be carefully monitored while patients are receiving clarithromycin and oral anticoagulants simultaneously. Elevated digoxin serum concentrations in patients receiving clarithromycin and digoxin concomitantly have also been reported in post-marketing surveillance. Some patients have shown clinical signs consistent with digoxin toxicity, including potentially fatal arrhythmias. Serum digoxin levels should be carefully monitored while patients are receiving digoxin and clarithromycin simultaneously. The following drug interactions, other than increased serum concentrations of carbamazepine and active acid metabolite of terfenadine, have not been reported in clinical trials with clarithromycin; however, they have been observed with erythromycin products and/or with clarithromycin in post-marketing experience. Concurrent use of erythromycin or clarithromycin and ergotamine or dihydroergotamine has been associated in some patients with acute ergot toxicity characterized by severe peripheral vasospasm and dysesthesia. Erythromycin has been reported to decrease the clearance of triazolam and, thus, may increase the pharmacologic effect of triazolam. There have been post-marketing reports of drug interactions and CNS effects (e.g., somnolence and confusion) with the concomitant use of clarithromycin and triazolam. There have been reports of an interaction between erythromycin and astemizole resulting in QT prolongation and torsades de pointes. Concomitant administration of erythromycin and astemizole is contraindicated. Because clarithromycin is also metabolized by cytochrome P450, concomitant administration of clarithromycin with astemizole is not recommended. As with other macrolides, clarithromycin has been reported to increase concentrations of HMG-CoA reductase inhibitors (e.g., lovastatin and simvastatin), through inhibition of cytochrome P450 metabolism of these drugs. Rare reports of rhabdomyolysis have been reported in patients taking these drugs concomitantly. The use of erythromycin and clarithromycin in patients concurrently taking drugs metabolized by the cytochrome P450 system may be associated with elevations in serum levels of these other drugs. There have been reports of interactions of erythromycin and/or clarithromycin with carbamazepine, cyclosporine, tacrolimus, hexobarbital, phenytoin, alfentanil, disopyramide, lovastatin, bromocriptine, valproate, terfenadine, cisapride, pimozide, rifabutin, and astemizole. Serum concentrations of drugs metabolized by the cytochrome P450 system should be monitored closely in patients concurrently receiving these drugs. | ||
| Toxicity | diarrhea, nausea, abnormal taste, dyspepsia, and abdominal discomfort. Pseudomembraneous colitis has been reported with clarithromycin use, Allergic reactions ranging from urticaria and mild skin eruptions to rare cases of anaphylaxis and Stevens-Johnson syndrome have occurred. Rare cases of severe hepatic dysfunctions also have been reported. Hepatic failure is usually reversible, but fatalities have been reported | ||
| Organisms Affected | Enteric bacteria and other eubacteria | ||
| Chemical IUPAC Name | 6-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-14-ethyl-12,13-dihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione | ||
| Chemical Formula | C38H69NO13 | ||
| Molecular Weight | 747.953 g/mol | ||
| Smiles String | CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC)C)C)O)(C)O | ||
| Melting Point | 217 - 220 °C | ||
| Water Solubility | 0.33 mg/L | ||
| State | solid | ||
| LogP/Hphobicity | 2.69 | ||
| Isoelectric Point | 8.99 | ||
| Biotransformation | hepatic | ||
| Half Life | 3-4 hours | ||
| Protein Binding [%] | low protein binding | ||
| RxList Link | RXlist | ||
| Sponsored links | |||
| Drug Reference |
http://www.drugs.com/cons/Clarithromycin.html http://www.rxlist.com/cgi/generic/clarith.htm | ||
| Drug Type | Approved Drug | ||
| Accession No | APRD00181 | ||
| CAS Registry Number | 81103-11-9 | ||
| KEGG Compound ID | C06912 | ||
| PubChem ID | SID:602963 | ||
| PharmGKB ID | Not Available | ||
| SwissProt ID | Not Available | ||
| GenBank ID | Not Available | ||
| Drug ID Number [DIN] | 2244756 |
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